Imidazolidinyl urea

Imidazolidinyl urea


IUPAC name Correct new structure (upper pic.): 1,1'-methylenebis{3-[1-(hydroxymethyl)-2,5-dioxoimidazolidin-4-yl]urea} Erroneous old structure (lower pic.): 1,1'-methylenebis{3-[3-(hydroxymethyl)-2,5-dioxoimidazolidin-4-yl]urea}
Other names Imidurea, Germall 115; N',N''-methylenebis[3-[1-(hydroxymethyl)- 2,5-dioxoimidazolidin-4-yl]urea]; 1-[1-(hydroxymethyl)-2,5-dioxoimidazolidin-4-yl]- 3-[[[1-(hydroxymethyl)-2,5-dioxoimidazolidin-4-yl] carbamoylamino]methyl]urea
Identifiers
CAS number	39236-46-9^Y= ^Y
PubChem	38258
ChemSpider	35067^Y
EC number	254-372-6
ChEBI	CHEBI:51805^Y
ChEMBL	CHEMBL65433^Y
Jmol-3D images	Image 1 Image 2
SMILES O=C2N(CO)C(NC(=O)NCNC(=O)NC1C(=O)NC(=O)N1CO)C(=O)N2 C(NC(=O)NC1C(=O)NC(=O)N1CO)NC(=O)NC2C(=O)NC(=O)N2CO
InChI InChI=1S/C11H16N8O8/c20-2-18-4(6(22)16-10(18)26)14-8(24)12-1-13-9(25)15-5-7(23)17-11(27)19(5)3-21/h4-5,20-21H,1-3H2,(H2,12,14,24)(H2,13,15,25)(H,16,22,26)(H,17,23,27)^Y Key: ZCTXEAQXZGPWFG-UHFFFAOYSA-N^Y InChI=1/C11H16N8O8/c20-2-18-4(6(22)16-10(18)26)14-8(24)12-1-13-9(25)15-5-7(23)17-11(27)19(5)3-21/h4-5,20-21H,1-3H2,(H2,12,14,24)(H2,13,15,25)(H,16,22,26)(H,17,23,27) Key: ZCTXEAQXZGPWFG-UHFFFAOYAS
Properties
Molecular formula	C₁₁H₁₆N₈O₈
Molar mass	388.29 g/mol
Y (verify) (what is: Y/N?) Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa)
Infobox references

Imidazolidinyl urea is an antimicrobial preservative used in cosmetics . It is chemically related to diazolidinyl urea which is used in the same way. Imidazolidinyl urea acts as a formaldehyde releaser.

Safety

Some people have a contact allergy to imidazolidinyl urea causing dermatitis.^[1] Such people are often also allergic to diazolidinyl urea.

Imidazolidinyl urea was poorly characterized until recently and still has a wrong CAS structure assigned to it. New data show that the hydroxymethyl functional group of the imidazolidine ring is attached to the carbon, not the nitrogen atom ^[2]:


Correct new structure	Erroneous old structure

Imidazolidinyl urea is produced by the chemical reaction of allantoin and formaldehyde in the presence of sodium hydroxide solution and heat. The reaction mixture is then neutralized with hydrochloric acid and evaporated:

2 + 3 H₂C=O →

Commercial imidazolidinyl urea is a mixture of different formaldehyde addition products including polymers.^[2]